Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach)

January 5, 20251hr 23min

Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach)

Lenny's Podcast: Product | Growth | Career

Alisa Cohn is an executive coach who works with C-suite executives at both startups and Fortune 500 companies. She was named one of the top 50 coaches globally and specializes in helping leaders have difficult conversations, build strong teams, and scale their companies effectively. In this episode, she shares specific scripts and frameworks for handling challenging leadership situations.
Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach)
Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach)
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Key Takeaways

  • Having difficult conversations is essential for being an effective leader, even though most people dread them
  • Focus on observable facts and data when giving feedback, not judgments or emotions
  • Your job as a leader isn't to make people happy - it's to drive results and help people grow
  • The "founder prenup" helps co-founders align on key issues before starting a company together
  • End every meeting with three key questions to ensure alignment and follow-through
  • Building trust and relationships makes difficult conversations easier over time

Introduction

Alisa Cohn is an executive coach who works with C-suite executives at both startups and Fortune 500 companies. She was named one of the top 50 coaches globally and specializes in helping leaders have difficult conversations, build strong teams, and scale their companies effectively. In this episode, she shares specific scripts and frameworks for handling challenging leadership situations.

Topics Discussed

Why We Avoid Difficult Conversations (4:48)

Most leaders dread difficult conversations because they:

  • Fear making people upset or sad
  • Worry about defensive reactions and having to deal with emotional fallout
  • Don't want to create additional drama or work to manage
  • Question if they might be wrong in their assessment

However, Alisa emphasizes that "through that upset, on the other side of that can often be a whole new possibility and a whole new revelation and actually a lot of joy and freedom."

Scripts for Performance Feedback (12:48)

When giving constructive feedback, Alisa recommends this basic script structure:

  • Start neutral: "I want to chat with you about [specific behavior/issue]"
  • Share observations: "What I'm hearing/observing is [specific examples]"
  • Connect to impact: "We both know that [why this matters]"
  • Focus on solutions: "Let's discuss how we can [desired outcome]"

Key elements that make the feedback more effective:

  • Focus on observable facts and data
  • Use "we" language to show partnership
  • Have a clear desired outcome
  • Keep tone matter-of-fact, not emotional

Handling Defensive Reactions (20:20)

If someone becomes defensive or emotional during feedback, Alisa suggests:

  • Pause the conversation and acknowledge the reaction
  • Reaffirm your positive intent to help them succeed
  • Offer to continue later if needed
  • Stay firm but compassionate about having the conversation

Sample script: "Let's pause for a second. I want you to know that I'm telling you this to help you succeed. I can see this is triggering some emotion. Would you like to continue now or should we pause and resume later?"

Scripts for Promotion Disappointment (25:07)

When delivering news about not getting a promotion:

  • Be direct upfront about the decision
  • Explain specific reasons why
  • Offer hope and path forward
  • Show you care about their career growth

Sample script: "I know this will be challenging to hear. We've decided to look externally for this role because [specific reasons]. I'm committed to helping you develop the skills needed and finding opportunities for your growth."

Scripts for Terminations (31:00)

Before terminating someone:

  • Ensure it's not a surprise through prior feedback
  • Be crystal clear about expectations and timeline
  • Document conversations and involve HR
  • Give concrete opportunity to improve

Sample warning script: "After six months of conversations about [issues], if these don't improve in 30 days, we'll need to part ways. I know you have it in you to change, but these are deal-breakers for the role."

The Importance of Positive Feedback (35:44)

Leaders should regularly give specific, meaningful positive feedback:

  • Build trust and relationships during good times
  • Be specific about what worked well
  • Connect behaviors to impact
  • Encourage continuation of good practices

Sample positive feedback: "The way you ran that launch was fantastic - your organization led to [specific benefits]. Keep doing that."

Understanding Your Job as a Leader (38:49)

Common leadership misconceptions:

  • Your job isn't to make people happy - it's to drive results
  • Avoiding conflict creates more problems long-term
  • Culture isn't just about fun perks - it's about how work gets done
  • Structure and process become necessary as companies scale

Three Questions to End Every Meeting (49:38)

To ensure alignment and follow-through, end meetings by asking:

  • "What did we decide here?" - Get explicit agreement
  • "Who needs to do what by when?" - Clear action items
  • "Who else needs to know?" - Communication plan

The Founder Prenup (55:57)

Key topics co-founders should align on upfront:

  • Core values and how they might conflict
  • Vision for success and exit goals
  • How to handle conflict and make decisions
  • Desired company culture and working styles
  • Work-life balance expectations

Conclusion

The key to being an effective leader is having the courage to have difficult conversations while maintaining relationships and trust. This requires:

  • Getting comfortable with discomfort
  • Using specific scripts and frameworks
  • Focusing on observable facts
  • Building trust through regular positive feedback
  • Having clear processes for decision-making and follow-through
  • Aligning on expectations upfront

By following these practices, leaders can create high-performing teams and companies while helping their people grow and succeed.

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